Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
expand_more
expand_more
format_list_bulleted
Question
Chapter 24, Problem 24.30P
Interpretation Introduction
Interpretation:
The coupling reaction and the staring material to form the given product has to be identified.
Concept Introduction:
Stille coupling uses a tin reagent (
Stille coupling gives conjugated dienes or alkenyl aryl system.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Only one of these statements about nucleophilic aromatic substitution is true.
O as the number of ortho and para electron withdrawing groups increases, the reaction rate decreases
O the reaction proceeds by an addition-elimination mechanism
the reaction involves a carbocation intermediate with delocalization of electrons
all are false
41. Zaitsev’s rule states that:
the alkene with less alkyl substituents is the major product in base-induced elimination reactions
the more highly substituted carbocation is formed as the intermediate rather than the less highly substituted one
the alkene with more alkyl substituents is the major product in base-induced elimination reactions
the less highly substituted carbocation is formed as the intermediate rather than the more highly substituted one
(dehydrobromination)
A chemist carried out an elimination reaction
of 1,1-dimethyl-2-
bromocyclopentane. The chemist expected the
reaction to yield alkene Z as product. However,
alkene Z DID NOT form. Instead, three alkenes
were produced: one alkene was the major
product, the other two alkenes was the minor
products.
What was the major alkene product that
formed?
Br
Select one:
A. I
B. II
C. IV
D. III
alcohol
HEAT
||
Z
=
+
(HBr)
IV
Chapter 24 Solutions
Organic Chemistry
Ch. 24.3 - Prob. 24.1PCh. 24.3 - Prob. 24.2PCh. 24.4 - Prob. 24.3PCh. 24.5 - Show how the following compound can be prepared...Ch. 24.5 - Prob. 24.5PCh. 24.5 - Prob. 24.6PCh. 24.6 - Prob. 24.7PCh. 24 - Prob. 24.8PCh. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Treatment of cyclohexene with iodobenzene under...Ch. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - The aryl diene undergoes sequential Heck reactions...Ch. 24 - Heck reactions take place with alkynes as well as...Ch. 24 - Prob. 24.16PCh. 24 - The following transformation involves a series of...Ch. 24 - Show the sequence of Heck reactions by which the...Ch. 24 - Prob. 24.19PCh. 24 - Write the steps that are critical in the following...Ch. 24 - Prob. 24.21PCh. 24 - Prob. 24.22PCh. 24 - Prob. 24.23PCh. 24 - Show how the following compound could be prepared...Ch. 24 - It is typically very difficult to do a...Ch. 24 - The compound eutypine is an antibacterial agent...Ch. 24 - Prob. 24.27PCh. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - Prob. 24.30PCh. 24 - Prob. 24.31PCh. 24 - Prob. 24.32PCh. 24 - Prob. 24.33PCh. 24 - The following transformation can be accomplished...Ch. 24 - Prob. 24.35PCh. 24 - Prob. 24.36PCh. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - E. J. Coreys 1964 total synthesis of...Ch. 24 - Prob. 24.40P
Knowledge Booster
Similar questions
- Do hydration reactions like this one have Markovnikov and anti-Markovnikov products? I know that for addition of halides on alkene double bonds, there are Markovnikov products becasue of 1,2-halide/methyl shifts, but there usually aren't shifts in hydration reactions. Essentially, would the Markovnikov/major product for this reaction have a hydroxy group attached to the tertiary carbocation and the anti-Markovnikov/minor product for this reaction have a hydroxy group attached to the adjacent secondary carbocation?arrow_forwardReaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?arrow_forwardWhat reaction presented in this chapter is occurring in the following equation? Explain the resulting stereochemistry of the reaction.arrow_forward
- When toluene is treated with sulfuric and nitric acids under special conditions, three nitro (NO2) groups are substituted for hydrogens at the 2, 4 and 6 positions on the ring (the next section discusses why the 2, 4, and 6 positions are substituted). The product is a highly explosive substance called 2,4,6-trinitrotoluene. This subastance is commonly known by a three letter name. What is it?arrow_forwardAlcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forwardHow could the following compound be prepared using an alkene as one of the starting materials? You can use the suitable reactives for this reaction.arrow_forward
- Draw the organic product that is expected to form when the following compound is oxidized under biological conditions. oxidation SH reduction • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • If no reaction occurs, draw the organic starting material.arrow_forward2. The following carbocation is generated as an intermediate in the addition of H-Br to an alkene. Draw the structure of all possible alkenes that could have formed this intermediate.arrow_forwardaddition of hbr to a double bond with an ether (-or) substituent occurs regiospecifically to give a product in which the Br OR are bonded to the same carbon. Draw the two possible carbocation intermediates in this electrophilic addition reaction,and explain using resonance why the observed product is formed.arrow_forward
- Draw the alkene that would react with the reagent given to account for the product formed. ? + + H₂O **** H₂S04 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. CH3 CH3 CHCCH3 | | OH CH3 +1arrow_forwardМЕСНANISMS 1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed opening of the epoxide ring to form two different products. > Using ethanol as the solvent and an appropriate acid, show the steps in the acid catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). > Using ethanol as the solvent and an appropriate base, show the steps in the base- catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). 1,2-epoxy-1-methylcyclopentane CH3arrow_forwardDraw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. CH3 CH3 H3PO4 HO, + H3C CH3 HO HO First stage in synthesis of the epoxy and polycarbonate ingredient bisphenol-A You do not have to consider stereochemistry. Include all valence lone pairs in your answer. In cases where there is more than one answer, just draw one.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning